


Jester's Day, Lover's Night

by ERS220



Category: Elder Scrolls, Elder Scrolls V: Skyrim
Genre: Blood, Blood Drinking, Cicero being Cicero, Cunnilingus, F/M, First Time, Loss of Virginity, Masturbation, Masturbation Interruptus, Oral Sex, Rough Sex, Virginity
Language: English
Status: Completed
Published: 2019-02-05
Updated: 2019-02-05
Packaged: 2019-10-22 14:22:31
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,321
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/17664311
Author URL: https://archiveofourown.org/users/ERS220/pseuds/ERS220
Summary: Iliana discovers a new meaning to Jester's Day.





	Jester's Day, Lover's Night

**Author's Note:**

> I'm back with more good 'ol self indulgent Cicero smut.

Do you know that unspeakable feeling? That deep warmth within your stomach that sends a shiver through your body when you think of them? Intense and unbearably hot. I had not known this feeling until I met my darling jester. Even then, I didn’t understand it. But that did not last for long.

The night in which our lips locked was deeply intense, but at the time, nothing had seemed to come of it. Neither I nor Cicero spoke of it after that, but his eyes occasionally met mine with power when others weren’t looking. No brothers or sisters knew of it, and they certainly wouldn’t ever as long as we were both alive. Weeks passed without much to speak of. A few dangerous contracts, hours spent reading books at night. However, the 28th of Rain’s Hand set forth change. Not to the brotherhood, but to Cicero and I, and who we were to one another.

A few days before, Astrid, the dark mistress of the family, had called upon me to speak with her as soon as possible. Anxiety welled within me, but I tried to keep myself calm before approaching her. I was unaware of what she needed from me, and my mind went to the worst possible scenarios. She glanced at me for a moment before looking back down at her map of Skyrim. “Iliana, I need you to do something important,” she began.  
“How shall I serve?” I asked, trying to hide the shake in my voice. My attempt to stifle it failed, and Astrid was quick to pick up on my feelings.  
“Calm down. You don’t need to work yourself up, it’s not a contract or anything like that. But it is important, like I said. Our food supply is getting low, and obviously we need more before we completely run out. Do you see what I’m getting at?” she asked. I nodded with a sigh of relief.  
“Good. If you couldn’t tell, I want you to do it. But I don’t want you going alone, considering how close to death you’ve gotten doing simple tasks,” she spoke with snide. “I want you to go with Cicero.”  
“Cicero?” I asked, furrowing my brow. I wasn’t upset, but curious. It seemed we always ended up together, one way or another.   
“Did I stutter? Yes, Cicero. He needs to do something for us. He hasn’t done much besides oiling the Night Mother, but that doesn’t benefit us, does it? He needs to understand that he has responsibilities while he’s here. Whether he knows that or not is a mystery to me, but I’m not going to sit around and just guess. I already told him about what’s happening, so you don’t have to tell him,” Astrid pointed to a dot on the map. “You’re going to Riften to get the food. The prices there are cheaper than Falkreathe. It’ll take a few days, but I expect you two to be back within a week. Just be careful. Jester’s day is coming up, and I don’t want you two to get caught in any traps or getting ripped off. Here’s the gold. Now go,” she said sternly, handing me a black leather bag with a fair amount of coin within. 

Within a few minutes, Cicero met me at the door to the sanctuary, humming a little happy tune. “Ah, good morning, Listener!”  
“Good morning, Cicero,” I replied quietly. I was feeling timid from Astrid’s words. It was clear she felt embarrassed at my recent incompetency, and I felt ashamed. I tried my very best, but even then it was not enough. At the very least, I would have time with Cicero in the coming days. He showed me respect I was unfamiliar with, and it was greatly appreciated. “Are you ready to head out?” I asked.  
“Yes, yes, of course! Cicero is always ready,” he chuckled. I didn’t know what he meant by that, but I brushed it off. Afterwards, we left the sanctuary and set our sights for Riften, the city of thieves.

Our journey was fairly short and quiet. We spoke little, and focused on the task at hand. I was determined to prove to Astrid that I wasn’t completely incompetent. As soon as we entered the city, I spent some of my own gold to get a room for the two of us at The Bee and Barb. Astrid had given us a fair amount of time to do a task as simple as shopping, and we had time to spend relaxing and resting our aching feet. Buying the food on the day before we left would benefit us greatly, as it would still be fresh. I didn’t admit it openly, but I hoped that this would please Astrid. 

The 26th and 27th passed, and then came Jester’s Day. Despite what was to come, the day started quietly, as had the rest. Cicero woke me up gently. My eyes fluttered open and the first thing I saw was his smiling face. It eased me, but at the time I was unsure as to why. Most people disliked him or even feared him, and felt unnerved by his mannerisms, but since that night weeks ago, they made me feel differently. Perhaps I unknowingly felt the comfort of a lover. “Good morning, Listener. Do you know what day it is?” he asked, his voice pitching upwards like it did when he was excited. “Jester’s Day! A day for dear, sweet Cicero! A day of tricks and jokes alike from and for the Fool of Hearts!” he exclaimed. I couldn’t help but smile a little at his delight. As I listened to him talk, I spent a fair amount of time looking him up and down, thinking of the night our lips intertwined. I felt my face become flushed as I remembered and examined the man in front of me. Although I hadn’t realized before, I found him incredibly attractive. Whether it was his kiss that swayed my opinion or not, my eyes lingered on his deep, dark eyes, chiseled features, and soft red hair that framed milky skin with light ginger freckles flecked upon his nose and cheeks. I had never noticed these details that adorned sweet Cicero before that day. He was quick to realize that I was staring at him, and he stopped for a moment, raising an eyebrow. “Is something wrong, Listener?” he asked.  
“Ah, no, sorry. I was… spacing out,” I sputtered. He seemed suspicious, but didn’t mention it again. He did, however, proceed talking, seeming to remember something.  
“Oh, Listener! I forgot to mention that I had plans to spend the day celebrating, but...” he stopped for a moment, looking at me. “...If you need Cicero, I shall spend the day serving the Listener, instead.”  
I was unaware that Cicero had made plans, as it wasn’t like him to do so without mentioning them, but my mind wandered to what I could do with a few hours of alone time. “Oh, no, no. It’s ok, go celebrate for as long as you want. It doesn’t bother me,” I smiled weakly. He then grabbed my shoulders in excitement.   
“Oh, so kind, so very kind! Thank you! I’ll be back later in the night. Thank you kind Listener!” he exclaimed, then rushing off before I could say goodbye. It didn’t bother me in the slightest, though. Seeing Cicero so happy, so genuinely happy, made me feel a warmth I hadn’t felt in a long time. 

The morning was spent reading, as per usual. As the day progressed, my mind began wandering back to Cicero. I kept pushing the thought of him away, but it was useless to resist. I couldn’t stop thinking of our kiss, his looks, how he had grabbed my shoulders. The thought of his touch was making me feel a strange heat within my body I hadn’t felt before. It grew in intensity the more I thought about the man. Before long, my mind wandered into the gutter. I was shocked at my own thoughts. I had never been one to think that way, let alone about another person, but I let it happen. The heat spread to my face, and I felt a distinct wetness grow in my nether region. I took a shaky hand and began to rub myself through my clothing, shivering and breathing heavily. I hadn’t masturbated in many years, and never felt a need to, but the thought of Cicero was driving me mad. After a bit, I threw off my clothes in the heat of the moment and continued touching myself, faster and rougher, sliding my fingers in and out with little control. I began to moan, and soon moaned the man’s name over and over without even thinking. Cicero. Oh, god, Cicero. I needed him in that moment, and it seemed like I would get my wish. “Listener?”

I froze in place at the sound of his voice. Reluctantly, I moved my eyes upwards to see him standing there, face incredibly flushed. There seemed to be blood on his clothing and a bit on his face, and a rip on his sleeve that also dripped with blood. We stared at each other for what seemed like eternity before I snapped out of it and hastily tried to cover myself, failing miserably. “Listener...why didn’t you tell dear Cicero you needed him that badly?” he asked, approaching me slowly. I wasn’t aware of how long he had been standing there, but there was a noticeable bulge within his pants. I tried to speak, but I couldn’t. I was still incredibly aroused and absolutely shocked at the same time, leaving me speechless. He took his gloves off and grabbed my chin, whispering into my ear. “How long have you wanted me, Iliana?” he asked. It was rare that he called me anything but listener, but that was the least of my concerns at the moment. He began to kiss my neck, leaving hickies all over it as he climbed on top of me. He moved the fur blankets from my body, exposing my skin once again. I melted into his kisses, letting instinct take hold. Before long, a wet spot formed on the bed where I was laying. I had never been this aroused in my entire life. Cicero noticed the spot, and then looked me in the eyes. “Do you want Cicero to take care of you?” his voice had lowered in pitch, and it made me shiver. I nodded slightly, then looking at the cut on his arm. I’m not sure what came over me, but I leaned over and licked the blood like a thirsty animal. His eyes widened a tad as he watched, and then he laughed when I had finished. I must have seemed so very desperate, being so eager to taste even the smallest bit of his flesh and blood, figuratively and literally. 

I could barely stand to look at him from sheer embarrassment, but at the same time, I couldn’t stop. Iliana Ashvanne, bearing her pale virgin flesh to Cicero, keeper of the Night Mother, Fool of Hearts. It felt so very strange. Cicero put his hands on my legs, and I instinctively spread them for him. He brought his face towards my slick, spreading the lips. I jolted at his touch, letting out a small yelp. It did not hurt, but the idea of someone other than myself touching such a delicate area gave me an adrenalin rush. He seemed to take in my scent, looking at me with desire I had never seen in his eyes. Cicero then began to lick and prod. As soon as he began, my ears began to ring, and the heat within my belly grew to a fever point. Although he had barely touched me, I came for the first time in my life. The man was taken aback at the sudden release, but continued to lick, drinking my orgasm like his life depended on it. He flicked my clit with his tongue before suckling on it. The pleasure was so intense after my I came that I couldn’t even moan, only breathe heavy breaths. Soon enough, I came again, and then again for Cicero. He seemed very pleased with himself, making someone such as the Listener tremble before him. He wiped his mouth with the back of his hand and then sat up, grabbing his bulge through his pants. He then pulled them down, exposing his hard rod. I could barely look at it, yet I wanted it. 

He stroked his cock on my slit before slowly beginning to push himself inside. It felt like his length was going to tear me in half. Cicero grunted slightly as he tried to push in further, it bearing difficult. It was then he realized I was a virgin, which seemed to drive him wild. After some more pushing and prodding, he managed to slide the rest in, hitting my cervix in the process. I yelled out in both pain and satisfaction. He then started to thrust hard and fast, which left me in ecstasy. Wrapping my legs around his waist, he got the hint that I was enjoying it, despite the fact that I was bleeding a bit. Cicero had completely taken over my body, humping so vigorously that beads of sweat dripped off his forehead and onto my chest. After ten, twenty more minutes, Cicero hitched and finally came, haphazardly pulling out at the last second. Despite this, I still felt some of his warm seed inside of me. Exhausted, he rolled over onto the other side of the bed, his chest raising and falling with hard, bated breaths. We lay without a word. All that could be said would not begin to describe how I was feeling at that moment on Jester’s Day. It was a night I would not soon forget.


End file.
